DD297951A5 - Verfahren zur herstellung von geminalen diarylalkanen, neue geminale diarylalkane und alk(en)ylierte aromaische verbindungen - Google Patents

Verfahren zur herstellung von geminalen diarylalkanen, neue geminale diarylalkane und alk(en)ylierte aromaische verbindungen Download PDF

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Publication number: DD297951A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; diarylalkanes; hydrogen; compounds; optionally substituted
Prior art date: 1989-05-20

Application number

DD90340776A

Other languages

German (de)

English (en)

Inventor

Dieter Arlt

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-05-20

Filing date

1990-05-17

Publication date

1992-01-30

1990-05-17 Application filed by ��@��k�� filed Critical ��@��k��

1992-01-30 Publication of DD297951A5 publication Critical patent/DD297951A5/de

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150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 28
238000000034 method Methods 0.000 title claims abstract description 24
-1 DIARYL ALKANES Chemical class 0.000 title claims abstract description 22
238000004519 manufacturing process Methods 0.000 title description 5
238000002360 preparation method Methods 0.000 claims abstract description 15
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
238000006243 chemical reaction Methods 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
238000005727 Friedel-Crafts reaction Methods 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000003107 substituted aryl group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000007791 liquid phase Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 15
239000000543 intermediate Substances 0.000 abstract description 5
238000003547 Friedel-Crafts alkylation reaction Methods 0.000 abstract description 2
239000004711 α-olefin Substances 0.000 abstract description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
238000003756 stirring Methods 0.000 description 25
239000012074 organic phase Substances 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000001273 butane Substances 0.000 description 13
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000004821 distillation Methods 0.000 description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
239000012043 crude product Substances 0.000 description 10
CEVQMSNVKOEJQE-UHFFFAOYSA-N 1,1,1,3-tetrachloro-3-methylbutane Chemical compound CC(C)(Cl)CC(Cl)(Cl)Cl CEVQMSNVKOEJQE-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 7
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000004305 biphenyl Substances 0.000 description 5
235000010290 biphenyl Nutrition 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000004508 fractional distillation Methods 0.000 description 5
229940078552 o-xylene Drugs 0.000 description 5
239000001294 propane Substances 0.000 description 5
QTKIQLNGOKOPOE-UHFFFAOYSA-N 1,1'-biphenyl;propane Chemical compound CCC.C1=CC=CC=C1C1=CC=CC=C1 QTKIQLNGOKOPOE-UHFFFAOYSA-N 0.000 description 4
MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 4
239000004642 Polyimide Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
229920001721 polyimide Polymers 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000005292 vacuum distillation Methods 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
125000006267 biphenyl group Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
FEKGWIHDBVDVSM-UHFFFAOYSA-N 1,1,1,2-tetrachloropropane Chemical class CC(Cl)C(Cl)(Cl)Cl FEKGWIHDBVDVSM-UHFFFAOYSA-N 0.000 description 2
ABHAVKJVPUIGGZ-UHFFFAOYSA-N 1-(4-chloro-2-methylbut-3-yn-2-yl)-4-methylbenzene Chemical compound ClC#CC(C)(C1=CC=C(C=C1)C)C ABHAVKJVPUIGGZ-UHFFFAOYSA-N 0.000 description 2
MWEGXROWCQZSDG-UHFFFAOYSA-N 1-methyl-4-(2-methylbut-3-yn-2-yl)benzene Chemical compound CC(C#C)(C)C1=CC=C(C=C1)C MWEGXROWCQZSDG-UHFFFAOYSA-N 0.000 description 2
DLUSTXUPBZDMOL-UHFFFAOYSA-N 1-phenoxy-4-[2-(4-phenoxyphenyl)propan-2-yl]benzene Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC=C1 DLUSTXUPBZDMOL-UHFFFAOYSA-N 0.000 description 2
BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 2
WWGUMAYGTYQSGA-UHFFFAOYSA-N 2,3-dimethylnaphthalene Chemical compound C1=CC=C2C=C(C)C(C)=CC2=C1 WWGUMAYGTYQSGA-UHFFFAOYSA-N 0.000 description 2
WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
VKEIPALYOJMDAC-UHFFFAOYSA-N 3,3,3-trichloroprop-1-ene Chemical class ClC(Cl)(Cl)C=C VKEIPALYOJMDAC-UHFFFAOYSA-N 0.000 description 2
JDICMOLUAHZVDS-UHFFFAOYSA-N 4-fluoro-3-phenoxybenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1OC1=CC=CC=C1 JDICMOLUAHZVDS-UHFFFAOYSA-N 0.000 description 2
WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000011814 protection agent Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000010457 zeolite Substances 0.000 description 2
HKNWNTZTFZALMT-UHFFFAOYSA-N (1,1-dichloro-3,4-dimethylpent-1-en-3-yl)benzene Chemical compound ClC(Cl)=CC(C)(C(C)C)C1=CC=CC=C1 HKNWNTZTFZALMT-UHFFFAOYSA-N 0.000 description 1
QFYLNISQQJUGPU-UHFFFAOYSA-N (4,4,4-trichloro-2-methylbutan-2-yl)benzene Chemical compound ClC(Cl)(Cl)CC(C)(C)C1=CC=CC=C1 QFYLNISQQJUGPU-UHFFFAOYSA-N 0.000 description 1
UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical class ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical compound ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 description 1
BRQJXNVTVVAYOW-UHFFFAOYSA-N 1,1-dichlorohept-1-en-3-ylbenzene Chemical compound CCCCC(C=C(Cl)Cl)C1=CC=CC=C1 BRQJXNVTVVAYOW-UHFFFAOYSA-N 0.000 description 1
XXZKEEJDKVIDMC-UHFFFAOYSA-N 1-(4-fluoro-3-phenoxyphenyl)-4-methyl-4-(4-methylphenyl)pent-2-yn-1-one Chemical compound FC1=C(C=C(C=C1)C(=O)C#CC(C)(C1=CC=C(C=C1)C)C)OC1=CC=CC=C1 XXZKEEJDKVIDMC-UHFFFAOYSA-N 0.000 description 1
JRHILJHOKDUQJF-UHFFFAOYSA-N 1-chloro-2-[2-(2-chlorophenyl)propan-2-yl]benzene Chemical compound C=1C=CC=C(Cl)C=1C(C)(C)C1=CC=CC=C1Cl JRHILJHOKDUQJF-UHFFFAOYSA-N 0.000 description 1
XINDACKDRJIBNF-UHFFFAOYSA-N 1-chloro-4-[2-(4-chlorophenyl)propan-2-yl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)C1=CC=C(Cl)C=C1 XINDACKDRJIBNF-UHFFFAOYSA-N 0.000 description 1
AODGGZSIKMISNU-UHFFFAOYSA-N 1-ethoxy-4-(4,4,4-trichloro-2-methylbutan-2-yl)benzene Chemical compound CCOC1=CC=C(C(C)(C)CC(Cl)(Cl)Cl)C=C1 AODGGZSIKMISNU-UHFFFAOYSA-N 0.000 description 1
RARBZNCQQVIVCU-UHFFFAOYSA-N 1-fluoro-4-[4-methyl-4-(4-methylphenyl)pentyl]-2-phenoxybenzene Chemical compound C1=CC(C)=CC=C1C(C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 RARBZNCQQVIVCU-UHFFFAOYSA-N 0.000 description 1
ZROJGLDKQRJURL-UHFFFAOYSA-N 1-methyl-2-[2-(2-methylphenyl)propan-2-yl]benzene Chemical compound CC1=CC=CC=C1C(C)(C)C1=CC=CC=C1C ZROJGLDKQRJURL-UHFFFAOYSA-N 0.000 description 1
PHRABVHYUHIYGY-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C([CH2])=CC=CC2=C1 PHRABVHYUHIYGY-UHFFFAOYSA-N 0.000 description 1
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
VSDONZKCFAWEHU-UHFFFAOYSA-N 1-phenoxy-4-(2-phenylpropan-2-yl)benzene Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 VSDONZKCFAWEHU-UHFFFAOYSA-N 0.000 description 1
BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 1
MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
PLLCCSYEGQDAIW-UHFFFAOYSA-N 5-ethyl-1,6-dimethyl-5-phenylcyclohexa-1,3-diene Chemical compound C=1C=CC=CC=1C1(CC)C=CC=C(C)C1C PLLCCSYEGQDAIW-UHFFFAOYSA-N 0.000 description 1
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
KCHNJJNSDCOIJY-UHFFFAOYSA-N C=1C=CC=CC=1C1(CCC)C=CC=CC1C Chemical compound C=1C=CC=CC=1C1(CCC)C=CC=CC1C KCHNJJNSDCOIJY-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
229920002821 Modacrylic Polymers 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910007926 ZrCl Inorganic materials 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000316 alkaline earth metal phosphate Inorganic materials 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
QPUYECUOLPXSFR-UHFFFAOYSA-N alpha-methyl-naphthalene Natural products C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000011552 falling film Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229960004279 formaldehyde Drugs 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229940094933 n-dodecane Drugs 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
238000010915 one-step procedure Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
150000000000 tetracarboxylic acids Chemical class 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
- C07C15/16—Polycyclic non-condensed hydrocarbons containing at least two phenyl groups linked by one single acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD90340776A 1989-05-20 1990-05-17 Verfahren zur herstellung von geminalen diarylalkanen, neue geminale diarylalkane und alk(en)ylierte aromaische verbindungen DD297951A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3916557A DE3916557A1 (de)	1989-05-20	1989-05-20	Verfahren zur herstellung von geminalen diarylalkanen, neue geminale diarylalkane und alk(en)ylierte aromatische verbindungen

Publications (1)

Publication Number	Publication Date
DD297951A5 true DD297951A5 (de)	1992-01-30

Family

ID=6381119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90340776A DD297951A5 (de)	1989-05-20	1990-05-17	Verfahren zur herstellung von geminalen diarylalkanen, neue geminale diarylalkane und alk(en)ylierte aromaische verbindungen

Country Status (5)

Country	Link
US (1)	US5136114A (fr)
EP (1)	EP0399284B1 (fr)
JP (1)	JPH0311024A (fr)
DD (1)	DD297951A5 (fr)
DE (2)	DE3916557A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3916557A1 (de) *	1989-05-20	1990-11-29	Bayer Ag	Verfahren zur herstellung von geminalen diarylalkanen, neue geminale diarylalkane und alk(en)ylierte aromatische verbindungen
DE59204022D1 (de) *	1991-02-22	1995-11-23	Bayer Ag	Verfahren zur Herstellung von 2,2-Bis-(3,4-dimethyl-phenyl)-propan.
US5977422A (en) *	1997-06-09	1999-11-02	The Dow Chemical Company	Organoaluminum catalysis of alkylation reactions

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2308419A (en) *	1941-03-12	1943-01-12	Dow Chemical Co	Method of making aralkyl iodides and corresponding alcohols
US2355850A (en) *	1942-06-20	1944-08-15	Dow Chemical Co	Method of making chlorobutyl-benzene compounds
US2485017A (en) *	1946-08-30	1949-10-18	Universal Oil Prod Co	Production of aryl dihaloalkanes
US2631172A (en) *	1948-01-29	1953-03-10	Universal Oil Prod Co	Preparation of aryl haloalkanes
US2654791A (en) *	1948-11-20	1953-10-06	Abbott Lab	Production of 2-chloro-1-phenylpropane
US3631211A (en) *	1970-04-20	1971-12-28	Universal Oil Prod Co	Preparation of gem-diarylalkanes
US3875249A (en) *	1971-03-10	1975-04-01	Ethyl Corp	Preparation of haloalkyl aromatic hydrocarbons
US4251675A (en) *	1979-03-15	1981-02-17	Uop Inc.	Preparation of diphenylmethane
US4365103A (en) *	1981-12-04	1982-12-21	The Dow Chemical Company	Process for the preparation of bis(1-phenylethenyl) compounds
DE3916452A1 (de) *	1989-05-20	1990-11-22	Bayer Ag	Verfahren zur herstellung von aromatischen alkanderivaten
DE3916557A1 (de) *	1989-05-20	1990-11-29	Bayer Ag	Verfahren zur herstellung von geminalen diarylalkanen, neue geminale diarylalkane und alk(en)ylierte aromatische verbindungen

1989
- 1989-05-20 DE DE3916557A patent/DE3916557A1/de not_active Withdrawn
1990
- 1990-04-30 US US07/516,629 patent/US5136114A/en not_active Expired - Fee Related
- 1990-05-08 EP EP90108628A patent/EP0399284B1/fr not_active Expired - Lifetime
- 1990-05-08 DE DE59009458T patent/DE59009458D1/de not_active Expired - Fee Related
- 1990-05-17 DD DD90340776A patent/DD297951A5/de not_active IP Right Cessation
- 1990-05-19 JP JP2130109A patent/JPH0311024A/ja active Pending

Also Published As

Publication number	Publication date
JPH0311024A (ja)	1991-01-18
EP0399284B1 (fr)	1995-08-02
DE3916557A1 (de)	1990-11-29
DE59009458D1 (de)	1995-09-07
EP0399284A2 (fr)	1990-11-28
US5136114A (en)	1992-08-04
EP0399284A3 (fr)	1991-11-27

Legal Events

Date	Code	Title	Description
1994-07-21	VZ	Disclaimer of patent (art. 11 and 12 extension act)

Publication	Publication Date	Title
DE3587304T2 (de)	1993-08-05	Herstellung von aromatischen carbonylverbindungen.
DE2646792A1 (de)	1977-04-28	Verfahren zur herstellung von alpha-(arylsubstituierten)-propionsaeuren
DE2457550C3 (de)	1982-02-04	Verfahren zur Herstellung von 1,1,3,4,4,6-Hexamethyl-1,2,3,4-tetrahydronaphthalin
DE4016895A1 (de)	1991-11-28	Verfahren zur herstellung von 1,4-bis-(4-fluorbenzoyl)-benzol
EP0064690B1 (fr)	1985-03-13	Procédé de préparation de benzaldéhydes substitués
DE1266754B (de)	1968-04-25	Verfahren zur Herstellung von 1, 1, 3, 4, 4, 6-Hexamethyl-1, 2, 3, 4-tetrahydronaphthalin
DD297951A5 (de)	1992-01-30	Verfahren zur herstellung von geminalen diarylalkanen, neue geminale diarylalkane und alk(en)ylierte aromaische verbindungen
DE2437882B2 (de)	1977-08-25	Verfahren zur herstellung von estern des 3-phenoxybenzylalkohols
DE1768624A1 (de)	1971-11-18	Verfahren zur Herstellung von Halogenphenylacetophenonen
EP0012224B1 (fr)	1989-01-18	Procédé de synthèse de mélanges de produits odorants
DE68906202T2 (de)	1993-11-25	Verfahren zur Herstellung von Arylethylphenolen mit einem (oder mehreren) Alkyl-Substituenten in der Ethylgruppe und deren Verwendung.
EP0396987A2 (fr)	1990-11-14	Trifluorométhylbenzaldéhydes fluorés dans le noyau
US2455643A (en)	1948-12-07	Condensation products from ketones and aralkyl organic compounds and method for producing the same
DE69404529T3 (de)	2001-02-01	Verfahren zur Herstellung von Cyclopentenonen
US3553274A (en)	1971-01-05	Process for the preparation of alkylated benzenes having halogen substituents in the 3,5- or 3,4,5-positions
EP0197274A1 (fr)	1986-10-15	Procédé pour la préparation de styrènes substitués
DE3877646T2 (de)	1993-06-24	Verfahren zur herstellung von p-alkylstyrolen.
CH500931A (de)	1970-12-31	Verfahren zur Herstellung von 2,4-disubstituierten Phenylketonen
US2158519A (en)	1939-05-16	Production of aromatic aldehydes
US4324929A (en)	1982-04-13	Process for producing mono, bis or tris(3,3,3-trifluoropropyl)benzene
DE69700036T2 (de)	1999-06-24	Verfahren zur Substitution von Cyclopentadien
DE2942894A1 (de)	1981-05-07	Verfahren zur herstellung von aromatischen aldehyden nach der sommelet-reaktion
DE69218898T2 (de)	1997-07-17	Verfahren zur Herstellung von Bisphenolen
US2961468A (en)	1960-11-22	Production of benzylacetophenones
EP0035186B1 (fr)	1983-05-04	Procédé pour la préparation du bromo-3 fluoro-4 toluène